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McDowell was born in Rossville, Tennessee. His parents, who were farmers, died in his youth. He started playing guitar at the age of 14 and played at dances around Rossville. Wanting a change from plowing fields, he moved to Memphis in 1926, where he worked in the Buck-Eye feed mill, which processed cotton into oil and other products.[5] He also had a number of other jobs and played music for tips. In 1928 he moved to Mississippi to pick cotton.[5] He finally settled in Como, Mississippi, about 40 miles south of Memphis, in 1940 or 1941 (or maybe the late 1950s), and worked steadily as a farmer, continuing to perform music at dances and picnics. Initially he played slide guitar, using a pocketknife and then a slide made from a beef rib bone, later switching to a glass slide for its clearer sound. He played with the slide on his ring finger.[6]

Although commonly regarded as a Delta blues singer, McDowell may be considered the first north hill country blues artist to achieve widespread recognition for his work. Musicians from the hill country – an area parallel to and east of the Delta region – produced a version of the blues somewhat closer in structure to its African roots. It often eschews chord change for the hypnotic effect of the droning single-chord vamp. McDowell's records offer glimpses of the style's origins, in the form of little-recorded supporting acts such as the string duo Bob and Miles Pratcher, the guitarist Eli Green, the fife player Napoleon Strickland, the harmonicist Johnny Woods and Hunter's Chapel Singers. McDowell's style (or at least its aesthetic) can be heard in the music of such hill country figures as Junior Kimbrough and R. L. Burnside, who in turn served as the impetus behind the creation of the Fat Possum record label in Oxford, Mississippi, in the 1990s.[7]

With a rising interest in blues and folk music in the United States in the 1950s, McDowell was brought to wider public attention, beginning when he was recorded in 1959 by Alan Lomax and Shirley Collins.[8] His records were popular, and he often performed at festivals and clubs.[9]

McDowell continued to perform blues in the north Mississippi style much as he had for decades, but he sometimes performed on electric guitar rather than acoustic guitar. While he famously declared, "I do not play no rock and roll," he was not averse to associating with younger rock musicians. He coached Bonnie Raitt on slide guitar technique[9] and was reportedly flattered by The Rolling Stones' rather straightforward version of his "You Gotta Move" on their 1971 album Sticky Fingers.[citation needed] In 1965 he toured Europe with the American Folk Blues Festival, together with Big Mama Thornton, John Lee Hooker, Buddy Guy, Roosevelt Sykes and others.[10]

McDowell's 1969 album I Do Not Play No Rock 'n' Roll, recorded in Jackson, Mississippi, and released by Malaco Records, was his first featuring electric guitar. It contains parts of an interview in which he discusses the origins of the blues and the nature of love. McDowell's final album,[11]Live in New York (Oblivion Records), was a concert performance from November 1971 at the Village Gaslight (also known as The Gaslight Cafe), in Greenwich Village, New York.

McDowell died of cancer in 1972, aged 66, and was buried at Hammond Hill Baptist Church, between Como and Senatobia, Mississippi. On August 6, 1993, a memorial was placed on his grave by the Mount Zion Memorial Fund. The ceremony was presided over by the blues promoter Dick Waterman, and the memorial with McDowell's portrait on it was paid for by Bonnie Raitt. The memorial stone was a replacement for an inaccurate and damaged marker (McDowell's name was misspelled). The original stone was subsequently donated by McDowell's family to the Delta Blues Museum, in Clarksdale, Mississippi. McDowell was a Freemason and was associated with Prince Hall Freemasonry; he was buried in Masonic regalia.[12]